Water → 1-(3-methyl-5-oxo-4H-imidazol-2-yl)-3-(6-oxo-1H-pyridin-2-yl)urea

HRID 904157Notes

Reaction equation

HRID 904157 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[N:8][C:9](=[O:11])O.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[N:14]=1.O>CN(C=O)C>[OH:19][C:15]1[N:14]=[C:13]([NH:12][C:9]([N:8]=[C:3]2[NH:4][C:5](=[O:7])[CH2:6][N:2]2[CH3:1])=[O:11])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 136469822tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene carbamic acidHCID 1785076342-Amino-6-hydroxypyridine

Product 1

HCID 1784811471-(3-methyl-5-oxo-4H-imidazol-2-yl)-3-(6-oxo-1H-pyridin-2-yl)ureaYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3.0 g (12.8 mM) of the phenyl carbamate 8 and 1.5 g (12.8 mM) of 2-amino-6-hydroxypyridine in 25 ml of anhydrous DMF was heated at 85° C. for 5 hrs., cooled, and poured into 100 ml of water. The resulting precipitate was collected, washed successively with water, ethanol, ethyl acetate, and ether. Recrystallization from ethanol gave 1.0 g of the above urea as a yellow solid, m.p. 233°-234° C. (dec.).

Workup

  1. temperature, cooled
  2. customThe resulting precipitate was collected
  3. washwashed successively with water, ethanol, ethyl acetate, and ether
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-ecb519eb07b84e7ba671f123b3c517f8
Source dataset
uspto-grants-1980_10
Patent number
US04230713

Reaction notes

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